The design flow of a digital cryptographic device must take into account the evaluation of its security against attacks based on side channels observation. The adoption of high level countermeasures, as well as the verification of the feasibility of new attacks, presently require the execution of timeconsuming physical measurements on the prototype product or the simulation at a low abstraction level. Starting from these assumptions, we developed an exploration approach centered on high level simulation, in order to evaluate the actual implementation of a cryptographic algorithm, being it software or hardware based. The simulation is performed within a unified tool based on SystemC, that can model a software implementation running on a microprocessor-based architecture or a dedicated hardware implementation as well as mixed software-hardware implementations with cycle-accurate resolution. Here we describe the tool and provide a large set of design explorations and characterizations based on actual implementations of the AES cryptographic algorithm, demonstrating how the execution of a large set of experiments allowed by the fast simulation engine can lead to important improvements in the knowledge and the identification of the weaknesses in cryptographic algorithm implementations.